Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 129, Issue 45, Pages 13794-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja075705g
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Total synthesis of the complex polycyclic indole alkaloid (+/-)-communesin F has been accomplished in 23 reaction steps in about 3% overall yield. The key steps relied on a highly efficient methodology for assembling the pentacyclic substructure 2 with the C7 quaternary carbon, the stereoselective preparation of the second C8 quaternary carbon by a two-step one-pot O-allylation and consecutive 3,3-rearrangement (2 to 3), and the stereoselective acid-catalyzed cyclization of 4 to form the azepine ring (5). These highly stereoselective reactions guaranteed the stereochemical results, allowing the construction of the C, E, F, and G ring systems.
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